A New α-Pyrone Derivative, 6-[(E)-Hept-1-enyl]-α-pyrone, with Tyrosinase Inhibitory Activity from a Marine Isolate of the Fungus Botrytis

Zhang, Dahai; Li, Xianguo; Kang, Jung Sook; Choi, Hong Dae; Son, Byeng Wha

doi:10.5012/bkcs.2007.28.5.887

Cited by 19 publications

(3 citation statements)

References 5 publications

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“…Interestingly, related α-pyrones were previously reported to be nontoxic or exhibited only moderate cytotoxicity against several cancer cell lines. 49 A number of α-pyrone analogues, however, revealed promising biological activities as antibacterial agents, 63 HIV-1 protease inhibitors, 64 tyrosinase inhibitors 65 or inhibitors of nitric oxide production, 47 making these metabolites attractive scaffolds for synthetic chemical studies. In our study, bulgarialactone B (1) revealed no cytotoxicity against the tested L5178Y cell line, albeit in a previous study it was reported to possess antitumor activity against an ascitic ovarian carcinoma xenograft.…”

Section: Resultsmentioning

confidence: 99%

Expanding the chemical diversity of an endophytic fungusBulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach

et al. 2019

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Section: Resultsmentioning

confidence: 99%

Expanding the chemical diversity of an endophytic fungusBulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach

et al. 2019

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“…Sibirinone 15a was isolated from Hypomyces semitranslucens , and 15b and 15c were reported as metabolite from strains of Trichoderma viride along with their elegant synthesis starting from propargyl bromide and propiolic acid . Additionally, 15c was found in the marine isolate of fungus Botrytis sp., while 15b is also a component of the queen recognition pheromone of fire ants Solenopsis invicta …”

Section: Resultsmentioning

confidence: 99%

Synthesis of 6-Substituted 2-Pyrones Starting from Renewable Resources: Total Synthesis of Sibirinone, (E)-6-(Pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(Hept-1-en-1-yl)-2H-pyran-2-one

Dobler

Reiser

2016

J. Org. Chem.

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An atom-economic reaction sequence to 6-substituted 2-pyrones was developed starting from furfuryl alcohol, a renewable resource made from bran or bagasse, and aldehydes, utilizing a thermal rearrangement of cyclopentadienone epoxides as key step. Derivatives bearing a hydroxyalkyl side chain could be enzymatically resolved, providing access to enantiomerically pure 2-pyrones, or converted to alkenyl-substituted 2-pyrones such as naturally occurring sibirinone, (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(hept-1-en-1-yl)-2H-pyran-2-one.

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“…which was obtained from the marine green alga Enteromorpha compressa, exhibited stronger anti-tyrosinase activity (IC 50 = 6.6 and 0.8 µM, respectively) than kojic acid (3, IC 50 = 7.7µM) [273]. The culture of the fungus Botrytis sp., isolated from the surface of the red seaweed Hyalosiphonia caespitosa, furnished 6-[(E)-hept-1-enyl]-α-pyrone (67) (Figure 10), which also exhibited more potent anti-tyrosinase activity than kojic acid (3) [274]. Culture of the marine sediment-derived Trichoderma viridae H1-7 produced homothallin II (68) (Figure 10), which is a competitive inhibitor of the mushroom tyrosinase.…”

Section: Marine Fungi-derived Compoundsmentioning

confidence: 99%

Marine-Derived Compounds with Potential Use as Cosmeceuticals and Nutricosmetics

et al. 2020

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The cosmetic industry is among the fastest growing industries in the last decade. As the beauty concepts have been revolutionized, many terms have been coined to accompany the innovation of this industry, since the beauty products are not just confined to those that are applied to protect and enhance the appearance of the human body. Consequently, the terms such as cosmeceuticals and nutricosmetics have emerged to give a notion of the health benefits of the products that create the beauty from inside to outside. In the past years, natural products-based cosmeceuticals have gained a huge amount of attention not only from researchers but also from the public due to the general belief that they are harmless. Notably, in recent years, the demand for cosmeceuticals from the marine resources has been exponentially on the rise due to their unique chemical and biological properties that are not found in terrestrial resources. Therefore, the present review addresses the importance of marine-derived compounds, stressing new chemical entities with cosmeceutical potential from the marine natural resources and their mechanisms of action by which these compounds exert on the body functions as well as their related health benefits. Marine environments are the most important reservoir of biodiversity that provide biologically active substances whose potential is still to be discovered for application as pharmaceuticals, nutraceuticals, and cosmeceuticals. Marine organisms are not only an important renewable source of valuable bulk compounds used in cosmetic industry such as agar and carrageenan, which are used as gelling and thickening agents to increase the viscosity of cosmetic formulations, but also of small molecules such as ectoine (to promote skin hydration), trichodin A (to prevent product alteration caused by microbial contamination), and mytiloxanthin (as a coloring agent). Marine-derived molecules can also function as active ingredients, being the main compounds that determine the function of cosmeceuticals such as anti-tyrosinase (kojic acid), antiacne (sargafuran), whitening (chrysophanol), UV protection (scytonemin, mycosporine-like amino acids (MAAs)), antioxidants, and anti-wrinkle (astaxanthin and PUFAs).

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A New α-Pyrone Derivative, 6-[(E)-Hept-1-enyl]-α-pyrone, with Tyrosinase Inhibitory Activity from a Marine Isolate of the Fungus Botrytis

Cited by 19 publications

References 5 publications

Expanding the chemical diversity of an endophytic fungusBulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach

Expanding the chemical diversity of an endophytic fungusBulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach

Synthesis of 6-Substituted 2-Pyrones Starting from Renewable Resources: Total Synthesis of Sibirinone, (E)-6-(Pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(Hept-1-en-1-yl)-2H-pyran-2-one

Marine-Derived Compounds with Potential Use as Cosmeceuticals and Nutricosmetics

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